In Season One, we meet Dobie Gillis (Dwayne Hickman), who is obsessed with impressing and winning over the girl of his dreams, the beautiful Thalia Menninger (Tuesday Weld). But he has to compete for her with the rich and snobby Milton Armitage (Warren Beatty) while keeping his beatnik buddy Maynard (Bob Denver) at bay and struggling with his parents (Frank Faylen, Florida Friebus) over money and his future. Meanwhile, the pushy and quirky Zelda (Sheila James) knows that she and Dobie are destined to be "a couple", whether Dobie realizes it or not.